4-methoxy-N-(3-phenylpropyl)benzenesulfonamide | 182565-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-N-(3-phenylpropyl)benzenesulfonamide
• CAS: 182565-30-6
• 化学式: C₁₆H₁₉NO₃S
• mdl: MFCD03231622
• 分子量: 305.398
• InChiKey: XEXZPBYTOCIDFN-UHFFFAOYSA-N

物化性质

• 沸点：
  464.3±55.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)
• 溶解度：
  40.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(3-phenylpropyl)benzenesulfonamide 在 四氢吡咯 、 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到3-苯基-1-丙胺
  参考文献：
  名称：

  SmI 2 /胺/水对甲苯磺酰胺和酯的瞬时脱保护

  摘要：

  SmI 2 /胺/水介导甲苯磺酰胺和甲苯磺酯的瞬时裂解。高度受阻，敏感和功能化的底物以接近定量的收率成功脱保护。

  DOI：

  10.1021/ol802243d
• 作为产物：
  描述：

  3-苯基-1-丙胺 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-methoxy-N-(3-phenylpropyl)benzenesulfonamide
  参考文献：
  名称：

  SmI 2 /胺/水对甲苯磺酰胺和酯的瞬时脱保护

  摘要：

  SmI 2 /胺/水介导甲苯磺酰胺和甲苯磺酯的瞬时裂解。高度受阻，敏感和功能化的底物以接近定量的收率成功脱保护。

  DOI：

  10.1021/ol802243d

文献信息

• Synthesis and Evaluation of 2-Alkylthio-4-(<i>N</i>-substituted sulfonamide)pyrimidine Hydroxamic Acids as Anti-myeloma Agents
  作者：Jinbao Xiang、Crystal Leung、Zhuoqi Zhang、Cassie Hu、Chao Geng、Lili Liu、Lang Yi、Zhiwei Li、James Berenson、Xu Bai

  DOI：10.1111/cbdd.12678

  日期：2016.3

  A series of pyrimidine hydroxamic acids with a sulfide substituent at the second position and a sulfonamide substituent at the fourth position have been synthesized and evaluated for their activity against human myeloma cell line RPMI 8226. Several compounds exhibited significant anti-cancer potency. It was found that representative compound 6a selectively killed cancerous but not normal cells. Moreover

  合成了一系列嘧啶异羟肟酸，在第二位具有硫化物取代基，在第四位具有磺酰胺取代基，并评估了它们对人骨髓瘤细胞系RPMI 8226的活性。几种化合物表现出显着的抗癌效力。发现代表性化合物6a选择性杀死癌细胞，但不杀死正常细胞。此外，化合物6a可有效引起RPMI 8226细胞凋亡，并显示出有希望的HDAC抑制活性。
• Cyclic amination onto aromatic ring of sulfonamides with (diacetoxyiodo)arenes: Effect of sulfonyl group
  作者：Hideo Togo、Yoichiro Hoshina、Masataka Yokoyama

  DOI：10.1016/0040-4039(96)01292-0

  日期：1996.8

  Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. The present reaction proceeded under mild and neutral conditions.

  用（二乙酰氧基碘）芳烃和碘在钨丝灯的照射条件下，用γ-二芳氧基碘处理伯胺在γ位带有芳环的磺酰胺，以中等至良好的产率得到相应的1,2,3,4-四氢喹啉衍生物。本反应在温和和中性条件下进行。
• Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits
  作者：Lawrence J. MacPherson、Erol K. Bayburt、Michael P. Capparelli、Brian J. Carroll、Robert Goldstein、Michael R. Justice、Lijuan Zhu、Shou-ih Hu、Richard A. Melton、Lynn Fryer、Ron L. Goldberg、John R. Doughty、Salvatore Spirito、Vincent Blancuzzi、Doug Wilson、Elizabeth M. O'Byrne、Vishwas Ganu、David T. Parker

  DOI：10.1021/jm960871c

  日期：1997.8.1

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.
• Oxidatively sonochemical dealkylation of various N-alkylsulfonamides to free sulfonamides and aldehydes
  作者：Masashi Katohgi、Hideo Togo

  DOI：10.1016/s0040-4020(01)00725-6

  日期：2001.8

  Various N-alkylsulfonamides were easily dealkylated to give the corresponding free sulfonamides in moderate to good yields in the presence of (diacetoxyiodo)benzene and iodine under ultrasonic irradiation. Application of this methodology to various AT-protected alkylamines with sulfonyl, phosphonyl, and acyl groups was carried out, and the oxidative conversion occurred only in N-sulfonyl-protected phenylalkylamines to give the corresponding aldehydes together with free sulfonamides in moderate to good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes
  作者：Hideo Togo、Yoichiro Hoshina、Takahito Muraki、Hiromasa Nakayama、Masataka Yokoyama

  DOI：10.1021/jo980450y

  日期：1998.7.1

  Sulfonamides of primary amines bearing an aromatic ring at the gamma-position were treated with (diacyloxyiodo)arenes and:iodine under irradiation conditions with;a tungsten-lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.